The Roland family moved to Flint January 23, 1923. Oliver attended Clark Elementary, Emerson Jr. High, and graduated from Flint Northern. He began playing softball at the age of ten. Mr. Eddie Robinson, a Hi-Y leader, organized a team and the youth sports activities at Roosevelt Elementary School in 1928. Oliver played the outfield and started to pitch. He developed into a promising young pitcher while playing for Fairview, a sandlot team.

Oliver was 15 years old when Mr. Simmons introduced him to Harold Johnson who was managing a team called the Pioneers. That introduction placed Oliver on the road to softball stardom. He became the outstanding pitcher for North Michigan, winning the City and District Championship and runners-up for the State Championship.

When Johnson organized the Yellow Dogs they became not only the talk of the town in softball but also the terror of Michigan softball opponents.

Dominating softball in the Flint area, he soon became known as “Twist” Roland because of his twisting motion in delivering his pitches. Oliver was now one of the best pitcher’s in Flint, with his good fastball, change-up floater and a dancing knuckler that kept batters off stride leading to many strikeouts. “Twist” soon became known as the strike out artist.

From 1935 through 1937 Roland averaged 15 strikeouts per game. He played in state tournaments in 1935, 36, 39, winning the state title in 1940.

He once pitched 36 games in one year. He won the most games in 1935, 36, 37 and pitched the most innings (over 200). He loved to pitch.

Oliver was a modest player and was well liked by teammates and the opposition alike. Once just before graduation, he took off his class robe long enough to pitch a shutout for the Yellow Dogs.

His career was dotted with no hitters, shutouts and many low hit games. During one stretch of victories he pitched 17 consecutive scoreless innings . With Oliver pitching, the Yellow Dogs won the 1940 State Championship. The next year he entered the Army. There he pitched on a team with some of the country’s best softball players. In the Central South Pacific Based Tournament, facing some of the best player’s from all over the United States, he was selected the tournament’s Most Valuable Player. After the war was over, Roland continued to pitch from time to time and retired from pitching at age fifty-eight.